(2E,4E,6E)-3-Methyl-7-(pyren-1-yl)octa-2,4,6-trienoic acid

Abstract

The title compound, C25H20O2, was synthesized by a Wittig reaction between triphenyl[1-(pyren-1-yl)ethyl]phosphonium bromide and ethyl (2E,4E)-3-methyl-6-oxohexa-2,4-dienoate, in the presence of n-butyl lithium, followed by saponification. It was obtained pure in the all-trans configuration following crystallization from ethyl acetate. The asymmetric unit contains two independent molecules (A and B), which are arranged almost parallel to each other within the crystal structure. The triene chain is not coplanar with the pyrene ring system, forming dihedral angles of 52.8 (1) and 42.2 (1)° for molecules A and B, respectively. Intermolecular hydrogen bonds between the carboxyl groups of the molecules link them into centrosymmetric pairs, AA and BB, each with the R22(8) graph-set motif.